Preparation of 2'-thio-2'-deoxycytidine 2' : 3'-phosphorothioate | Zendy

E. Morton Bradbury | Zendy; Joseph Nagyváry | Zendy

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Preparation of 2'-thio-2'-deoxycytidine 2' : 3'-phosphorothioate

Author(s) -

E. Morton Bradbury,

Joseph Nagyváry

Publication year - 1976

Publication title -

nucleic acids research

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/3.10.2437

Subject(s) - deoxycytidine , ribonucleotide , biology , thio , stereochemistry , thymidine , reactivity (psychology) , intramolecular force , dna , biochemistry , nucleotide , chemistry , genetics , chemotherapy , medicine , alternative medicine , pathology , gemcitabine , gene

The synthesis of a novel ribonucleotide analog 2'-thio-2' deoxycytidine 2':3'-O,S-phosphorothioate is described. In the first step, 2,2'-anhydro 1-beta-D-arabinosylcytosine was thiophosphorylated by the action of dithiophosphate, a process which gave predominantly the 3'-O-phosphorothioate isomer. An intramolecular displacement reaction led to the formation of the title compound. Structure and reactivity of this thioanalog differ substantially from 2':3'-CMP.

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